Absolutely. I’ve got flip flops that cost more than a dinner at a nice restaurant. And my feet are always freshly pedicured. Big difference than a guy with ugly feet wearing beat up Old Navy style flip flops.
Of course, we’re not in the South and it’s not 50 years ago. We live in 2017, in Southern California, land of Hollywood and beaches, where designer flip flops make sense. Would I wear designer flip flops to Providence? No. Would I wear them to Nobu Malibu? Yes.
I think it would be odd to hold people to manners/customs/norms from a different part of the country/world and/or social norms from years ago.